Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3

Detalhes bibliográficos
Autor(a) principal: Godoi, Marla Narciso
Data de Publicação: 2005
Outros Autores: Costenaro, Hellen S., Kramer, Eliane, Machado, Paola S., D'Oca, Marcelo Gonçalves Montes, Russowsky, Dennis
Tipo de documento: Artigo
Idioma: por
Título da fonte: Repositório Institucional da UFRGS
Texto Completo: http://hdl.handle.net/10183/72847
Resumo: In this paper, we describe a practical route for the synthesis of Biginelli compounds using In(OTf)3. To study the generality of this catalyst, several examples using aromatic aldehydes, 1,3-dicarbonyl compounds, urea, and thiourea were investigated. The present procedure provides an efficient modification of the classical Biginelli reaction, namely short reaction times and simple work-up, that not only preserves the simplicity of the original protocol but also produces excellent yields of 3,4-dihydropyridin-2(1H)-ones. Thiourea was used with similar success to provide the corresponding 3,4-dihydropyridin-2(1H)-thiones. In this case, the (+/-)-monastrol, antimitotic agent, was obtained in 92% yield and new thio analogues were synthesized.
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spelling Godoi, Marla NarcisoCostenaro, Hellen S.Kramer, ElianeMachado, Paola S.D'Oca, Marcelo Gonçalves MontesRussowsky, Dennis2013-07-02T01:43:08Z20050100-4042http://hdl.handle.net/10183/72847000525656In this paper, we describe a practical route for the synthesis of Biginelli compounds using In(OTf)3. To study the generality of this catalyst, several examples using aromatic aldehydes, 1,3-dicarbonyl compounds, urea, and thiourea were investigated. The present procedure provides an efficient modification of the classical Biginelli reaction, namely short reaction times and simple work-up, that not only preserves the simplicity of the original protocol but also produces excellent yields of 3,4-dihydropyridin-2(1H)-ones. Thiourea was used with similar success to provide the corresponding 3,4-dihydropyridin-2(1H)-thiones. In this case, the (+/-)-monastrol, antimitotic agent, was obtained in 92% yield and new thio analogues were synthesized.application/pdfporQuímica nova. São Paulo. Vol. 28, n. 6 (nov./dez. 2005), p. 1010-1013Síntese orgânicaMonastrol(+/-)-monastrolLewis acidMulticomponent reactionSíntese do monastrol e novos compostos de biginelli promovida por In(OTf)3Synthesis of monastrol and of new biginelli compounds promoted by in(otf)3 info:eu-repo/semantics/articleinfo:eu-repo/semantics/otherinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFRGSinstname:Universidade Federal do Rio Grande do Sul (UFRGS)instacron:UFRGSORIGINAL000525656.pdf000525656.pdfTexto completoapplication/pdf135073http://www.lume.ufrgs.br/bitstream/10183/72847/1/000525656.pdf09fee684e8ab53370b6ac7fa896a21d8MD51TEXT000525656.pdf.txt000525656.pdf.txtExtracted Texttext/plain20744http://www.lume.ufrgs.br/bitstream/10183/72847/2/000525656.pdf.txtc25c14dd0bb12042194e7e7e91db0736MD52THUMBNAIL000525656.pdf.jpg000525656.pdf.jpgGenerated Thumbnailimage/jpeg1909http://www.lume.ufrgs.br/bitstream/10183/72847/3/000525656.pdf.jpga9c207e9209e85abf3cfadc3a6873afdMD5310183/728472019-03-20 02:30:47.341325oai:www.lume.ufrgs.br:10183/72847Repositório de PublicaçõesPUBhttps://lume.ufrgs.br/oai/requestopendoar:2019-03-20T05:30:47Repositório Institucional da UFRGS - Universidade Federal do Rio Grande do Sul (UFRGS)false
dc.title.pt_BR.fl_str_mv Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
dc.title.alternative.en.fl_str_mv Synthesis of monastrol and of new biginelli compounds promoted by in(otf)3
title Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
spellingShingle Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
Godoi, Marla Narciso
Síntese orgânica
Monastrol
(+/-)-monastrol
Lewis acid
Multicomponent reaction
title_short Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
title_full Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
title_fullStr Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
title_full_unstemmed Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
title_sort Síntese do monastrol e novos compostos de biginelli promovida por In(OTf)3
author Godoi, Marla Narciso
author_facet Godoi, Marla Narciso
Costenaro, Hellen S.
Kramer, Eliane
Machado, Paola S.
D'Oca, Marcelo Gonçalves Montes
Russowsky, Dennis
author_role author
author2 Costenaro, Hellen S.
Kramer, Eliane
Machado, Paola S.
D'Oca, Marcelo Gonçalves Montes
Russowsky, Dennis
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Godoi, Marla Narciso
Costenaro, Hellen S.
Kramer, Eliane
Machado, Paola S.
D'Oca, Marcelo Gonçalves Montes
Russowsky, Dennis
dc.subject.por.fl_str_mv Síntese orgânica
Monastrol
topic Síntese orgânica
Monastrol
(+/-)-monastrol
Lewis acid
Multicomponent reaction
dc.subject.eng.fl_str_mv (+/-)-monastrol
Lewis acid
Multicomponent reaction
description In this paper, we describe a practical route for the synthesis of Biginelli compounds using In(OTf)3. To study the generality of this catalyst, several examples using aromatic aldehydes, 1,3-dicarbonyl compounds, urea, and thiourea were investigated. The present procedure provides an efficient modification of the classical Biginelli reaction, namely short reaction times and simple work-up, that not only preserves the simplicity of the original protocol but also produces excellent yields of 3,4-dihydropyridin-2(1H)-ones. Thiourea was used with similar success to provide the corresponding 3,4-dihydropyridin-2(1H)-thiones. In this case, the (+/-)-monastrol, antimitotic agent, was obtained in 92% yield and new thio analogues were synthesized.
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dc.date.issued.fl_str_mv 2005
dc.date.accessioned.fl_str_mv 2013-07-02T01:43:08Z
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dc.identifier.uri.fl_str_mv http://hdl.handle.net/10183/72847
dc.identifier.issn.pt_BR.fl_str_mv 0100-4042
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url http://hdl.handle.net/10183/72847
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dc.relation.ispartof.pt_BR.fl_str_mv Química nova. São Paulo. Vol. 28, n. 6 (nov./dez. 2005), p. 1010-1013
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